Chromene compound

Abstract

The present invention relates to a novel chromene compound having favorable photochromic properties, developing a color of a high density, exhibiting a small degree of initial color and permitting the color to quickly fade. The novel chromene compound has an amino group that may be substituted for a sixth position of a naphthopiran ring, has electron-donating groups at para-positions of the two phenyl groups bonded to the third position, and has at least one or more electron-attracting groups at meta-positions of the phenyl groups, and is represented, for example, by the following formula, ##STR1##

Claims

1. A chromene compound represented by the following general formula (1), ##STR49## wherein X is an amino group represented by the following formula (2),

wherein R1 and R2 may be the same or different, and are hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups or hetero rings, having 6 to 10 carbon atoms,

2. A chromene compound according to claim 1, wherein said substituent X has 3 to 6 carbon atoms for constituting a ring, said ring may have a hetero atom selected from an oxygen atom, a sulfur atom or a nitrogen atom, and said ring is a cyclic amino group in which a hetero ring or an aromatic ring may be condensed.

3. A chromene compound according to claim 2, wherein said cyclic amino group is a morpholino group, a thiomorpholino group, an N-methylpiperazinyl group, an indolinyl group or a tetrahydroquinolinyl group.

4. A chromene compound according to claim 1, wherein said substituents Y1 and Y2 may be different from each other, and are alkyl groups, alkoxyl groups, alkoxyalkyl groups, aralkyl groups, substituted or unsubstituted amino groups, aryloxyl groups or acyloxyl groups.

5. A chromene compound according to claim 1, wherein said substituents Y1 and Y2 may be different from each other, and are alkyl groups, alkoxyl groups, alkoxyalkyl groups or aryloxyl groups.

6. A chromene compound according to claim 1, wherein among said substituents Z1, Z2, Z3 and Z4, one or two are electron-attracting groups.

7. A chromene compound according to claim 6, wherein said electron-attracting group is at least the one selected from the group consisting of a halogen atom, a trifluoromethyl group, a cyano group, a nitro group, an alkoxycarbonyl group and an acyl group.

8. A chromene compound according to claim 6, wherein said electron-attracting group is at least the one selected from the group consisting of a halogen atom, a trifluoromethyl group, a cyano group and an alkoxycarbonyl group.

9. A chromene compound according to claim 1, wherein said substituent X is a morpholino group, a thiomorpholino group, an N-methylpiperazinyl group, an indolinyl group or a tetrahydroquinolinyl group, and said substituents Y1 and Y2 may be different from each other, and are alkyl groups, alkoxyl groups, alkoxyalkyl groups or aryloxyl groups, and at least one of said substituents Z1, Z2, Z3 and Z4 are at least the electron-attracting groups selected from the group consisting of a halogen atom, a trifluoromethyl group, a cyano group and an alkoxycarbonyl group.

10. A chromene compound according to claim 1, wherein substituent exists at none of the fifth position, seventh position, eighth position, ninth position or tenth position of said naphthopyran ring.

11. A chromene compound according to claim 1, wherein a total of not more than three substituents are bonded to carbon at any of the fifth position, seventh position, eighth position, ninth position or tenth position of said naphthopyran ring.

12. A chromene compound according to claim 11, wherein said substituent is an alkyl group, an alkoxyl group, an aralkyl group, an acyl group, an alkoxycarbonyl group, a substituted amino group, an aryl group, an acyloxyl group, a nitro group, a hydroxyl group, a cyano group or a halogen atom.

13. A chromene compound according to claim 1, comprising a 3,3-bis(3-fluoro-4-methoxyphenyl)-6-morpholino-3H-benzo (f) chromene.

14. A chromene compound according to claim 1, comprising a 3-(3,5-difluoro-4-methoxyphenyl)-3-(4methoxyphenyl)-6-morpholino-3H-benzo (f) chromene.

15. A chromene compound according to claim 1, comprising a 3,3-bis(3-fluoro-4-methoxyphenyl)-6-(2-methylindolinyl)-3H-benzo (f) chromene.

16. A chromene compound according to claim 1, comprising a 3-(3-fluoro-4-methoxyphenyl)-3-(4-methoxymethylphenyl)-6-(tetrahydroquinol inyl)-3H-benzo (f) chromene.

17. A chromene compound according to claim 1, comprising a 3-(3-chloro-4-methylphenyl)-3-(4-methoxyphenyl)-6-(tetrahydroquinolinyl)-3 H-benzo (f) chromene.

18. A chromene compound according to claim 1, comprising a 3-(3-chloro-4-(2-methoxyethoxy)phenyl)-3-(3-fluoro-4-methoxyphenyl)-6-morp holino-3H-benzo (f) chromene.

19. A chromene compound according to claim 1, comprising a 3-(3-bromo-4-methoxyphenyl)-3-(3-chloro-4-methoxyphenyl)-6-thiomorpholino- 3H-benzo (f) chromene.

20. A chromene compound according to claim 1, comprising a 3-(4-t-butoxyphenyl)-3-(3-trifluoromethyl-4-methoxyphenyl)-6-indolinyl-3H- benzo (f) chromene.

21. A chromene compound according to claim 1, comprising a 3-(3-chloro-4-methoxyphenyl)-3-(3-methoxycarbonyl-4-isopropoxyphenyl)-6-mo rpholino-3H-benzo (f) chromene.

22. A chromene compound according to claim 1, comprising a 3-(3-cyano-4-methoxyphenyl)-3-(4-methoxyphenyl)-6-morpholino-3H-benzo (f) chromene.

23. A chromene compound according to claim 1, comprising a 3-(3-chloro-4-phenoxyphenyl)-3-(3-fluoro-4-methoxyphenyl)-6-(4-N-methylpip eradinyl)-3H-benzo (f) chromene.

24. A chromene compound according to claim 1, comprising a 3,3-bis(3-fluoro-4-methoxyphenyl)-6-thiomorpholino-3H-benzo (f) chromene.